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[ CAS No. 37904-72-6 ] {[proInfo.proName]}

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Chemical Structure| 37904-72-6
Chemical Structure| 37904-72-6
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Product Details of [ 37904-72-6 ]

CAS No. :37904-72-6 MDL No. :MFCD06409221
Formula : C10H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :YWNKTZFJKMGVRP-UHFFFAOYSA-N
M.W : 242.11 Pubchem ID :142225
Synonyms :

Calculated chemistry of [ 37904-72-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.71
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.89
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 2.17
Log Po/w (SILICOS-IT) : 2.3
Consensus Log Po/w : 2.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.31
Solubility : 0.12 mg/ml ; 0.000495 mol/l
Class : Soluble
Log S (Ali) : -2.98
Solubility : 0.255 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0461 mg/ml ; 0.000191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 37904-72-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37904-72-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 37904-72-6 ]
  • Downstream synthetic route of [ 37904-72-6 ]

[ 37904-72-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 210832-81-8 ]
  • [ 37904-72-6 ]
YieldReaction ConditionsOperation in experiment
89% With Diethyl phosphonate; triethylamine In tetrahydrofuran at 0 - 20℃; for 6 h; In 30 ml of THF was dissolved 2 (5.1 g, 1 eq), then at 0° C. was added dropwise a mixture of diethylphosphite (2.04 ml, 1 eq) and Et3N (2.4 ml, 1.1 eq) in 12 ml of THF. The resulting mixture was stirred 6 h at RT, then evaporated and poured into 200 ml of ice/H2O and the resulting precipitated was filtered, washed with H2O and dried in vacuum. 3 was obtained as a green solid in 89percent yield. NMR 1H (CDCl3), δ=2.97 (s, 6H, 2CH3); 4.45 (s, 2H, CH2); 6.57 (d, 2H, J=9.0 Hz, 2CHAr); 7.72 (d, 2H, CHAr). NMR 13C (CDCl3), δ=31.3 (1C, CH2); 40.4 (2C, CH3); 111.1 (2C, CHAr); 121.8 (1C, Cq); 131.6 (2C, CHAr); 154.1 (1C, Cq); 189.7 (1C, Cq); In 30 ml of THF was dissolved 2 (5.1 g, 1 eq), then at 0° C. was added dropwise a mixture of diethylphosphite (2.04 ml, 1 eq) and Et3N (2.4 ml, 1.1 eq) in 12 ml of THF. The resulting mixture was stirred 6 h at RT, then evaporated and poured into 200 ml of ice/H2O and the resulting precipitated was filtered, washed with H2O and dried in vacuum. 3 was obtained as a green solid in 89percent yield. NMR 1H (CDCl3), δ=2.97 (s, 6H, 2CH3); 4.45 (s, 2H, CH2); 6.57 (d, 2H, J=9.0 Hz, 2CHAr); 7.72 (d, 2H, CHAr). NMR 13C (CDCl3), δ=31.3 (1C, CH2); 40.4 (2C, CH3); 111.1 (2C, CHAr); 121.8 (1C, Cq); 131.6 (2C, CHAr); 154.1 (1C, Cq); 189.7 (1C, Cq).
65.5% With Diethyl phosphonate; triethylamine In tetrahydrofuran at 0 - 20℃; To 13 tetrahydrofuran (40 mL) was added 14 2,2-dibromo-1-(4-(dimethylamino)phenyl)ethanone (6.84 g, 21.5 mmol) synthesized in the step 1-1, to which was then slowly added a solution of 15 diethyl phosphite (3 mL) and 16 triethylamine (3.2 mL) in tetrahydrofuran (25 mL) at 0° C. through a dropping funnel. The resultant was stirred at room temperature for 11 hours. The solvent was distilled off under reduced pressure for concentration, and the residue was added to 10 water cooled with ice, which was then stirred for 0.5 hour. The resultant solid was collected by filtration and washed with water cooled with ice to provide (17 2) in the scheme 1 (yield: 3.38 g (65.5percent)). [0051] 1H-NMR (400 MHz, deuterated chloroform) δ 7.89 (d, J=8.8 Hz, 2H), 6.66 (d, J=8.8 Hz, 2H), 4.36 (s, 2H), 3.08 (s, 6H).
63% With Diethyl phosphonate; triethylamine In tetrahydrofuran at 0 - 20℃; for 6 h; . To a stirred solution of 83-1 (1.76 g, 5.60 mmol) in THF (10 mL) was added the solution of (EtO)2POH (812 mg, 5.88 mmol) and TEA (594 mg, 5.88 mmol) in THF (5 mL) at 0 0 C dropwise. The mixture was gradually warmed to r.t. and stirred for 6 h. The resultant was concentrated and poured into ice/water. The formed precipitate was collected by filtration, washed with water and air-dried to afford the pure 83-2 (850 mg, 63 percent) as a yellow solid.
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 28, p. 4987 - 4990
[2] Patent: US2007/258887, 2007, A1, . Location in patent: Page/Page column 28; 39-40
[3] Chemical Communications, 2016, vol. 52, # 90, p. 13277 - 13280
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2966 - 2968
[5] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 7, p. 596 - 600
[6] Patent: US2014/88306, 2014, A1, . Location in patent: Paragraph 0050-0051
[7] Patent: WO2015/200619, , A1, . Location in patent: Paragraph 0272[7] Patent: , 2015, , . Location in patent: Paragraph 0272
[9] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S29 - S32
[10] Journal of the Chemical Society, Dalton Transactions, 2002, vol. 2, # 1, p. 48 - 54
[11] Journal of the American Chemical Society, 2009, vol. 131, # 46, p. 16663 - 16665
[12] Patent: WO2013/82508, 2013, A1, . Location in patent: Sheet 9/10
  • 2
  • [ 2124-31-4 ]
  • [ 37904-72-6 ]
Reference: [1] European Journal of Organic Chemistry, 2007, # 29, p. 4831 - 4836
[2] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1095 - 1105
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 30, p. 7268 - 7274
[4] Yakugaku Zasshi, 1955, vol. 75, p. 54[5] Chem.Abstr., 1956, p. 864
[6] Journal of the Chemical Society, Dalton Transactions, 2002, vol. 2, # 1, p. 48 - 54
[7] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S29 - S32
[8] Tetrahedron Letters, 1998, vol. 39, # 28, p. 4987 - 4990
[9] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2966 - 2968
[10] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 14, p. 4193 - 4196
[11] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 7, p. 596 - 600
[12] Patent: WO2013/82508, 2013, A1,
[13] Patent: US2014/88306, 2014, A1,
[14] Patent: WO2015/200619, , A1, [14] Patent: , 2015, ,
  • 3
  • [ 2124-31-4 ]
  • [ 37904-72-6 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 28, p. 4987 - 4990
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